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Polyvinylpyridine-Supported Palladium Nanoparticles: A Valuable Catalyst for the Synthesis of Alkynyl Ketones via Acyl Sonogashira Reactions

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Abstract

Palladium nanoparticles (NP) immobilized on metal scavengers (Smopex®-234, Smopex®-111, PVPy, 1% w/w) have been tested in the acyl Sonogashira reactions between terminal acetylenes and acid chlorides. Pd/PVPy resulted especially effective in the synthesis of alkynyl ketones with different stereoelectronic properties, even working with a very low amount of palladium (0.2 mol%). Preliminary tests seem to indicate that Pd/PVPy could act as a reservoir of very active palladium NP which are partially released during the reaction and then recaptured from the resin at the end of the process, thus ensuring the possibility of reuse of the catalyst.

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References

  1. Edwards ML, Stemerick DM, Sunkara PS (1990) J Med Chem 33:1948–1954

    Article  CAS  PubMed  Google Scholar 

  2. Chowdhury C, Kundu NG (1999) Tetrahedron 55:7011–7016

    Article  CAS  Google Scholar 

  3. Kundu NG, Mahanty JS, Chowdhury C, Dasgupta SK, Das B, Spears CP, Balzarini J, De Clercq E (1999) Eur J Med Chem 34:389–398

    Article  CAS  Google Scholar 

  4. Quesnelle CA, Gill P, Dodier M, St. Laurent D, Serrano-Wu M, Marinier A, Martel A, Mazzucco CE, Stickle TM, Barrett JF, Vyas DM, Balasubramanian BN (2003) Bioorg Med Chem Lett 13:519-524

  5. Rao PNP, Chen Q-H, Knaus EE (2005) Bioorg Med Chem Lett 15:4842–4845

    Article  CAS  PubMed  Google Scholar 

  6. Rao PNP, Chen Q-H, Knaus EE (2006) J Med Chem 49:1668–1683

    Article  CAS  PubMed  Google Scholar 

  7. Kuklev DV, Domb AJ, Dembitsky VM (2013) Phytomedicine 20:1145–1159

    Article  CAS  PubMed  Google Scholar 

  8. Takashima A, English B, Chen Z, Cao J, Cui R, Williams RM, Faller DV (2014) ACS Chem Biol 9:1003–1014

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  9. Karpov AS, Müller TJJ (2003) Org Lett 5:3451–3454

    Article  CAS  PubMed  Google Scholar 

  10. Karpov AS, Merkul E, Oeser T, Müller TJJ (2005) Chem Commun 2581-2583

  11. Karpov AS, Rominger F, Müller TJJ (2005) Org Biomol Chem 3:4382–4391

    Article  CAS  PubMed  Google Scholar 

  12. Karpov AS, Merkul E, Oeser T, Müller TJJ (2006) Eur J Org Chem 2006:2991–3000

    Article  CAS  Google Scholar 

  13. Zhou C, Dubrovsky AV, Larock RC (2006) J Org Chem 71:1626–1632

    Article  CAS  PubMed  Google Scholar 

  14. Palimkar SS, More VS, Srinivasan KV (2008) Synth Commun 38:1456–1469

    Article  CAS  Google Scholar 

  15. Willy B, Dallos T, Rominger F, Schönhaber J, Müller TJJ (2008) Eur J Org Chem 2008:4796–4805

    Article  CAS  Google Scholar 

  16. Willy B, Müller TJJ (2008) Eur J Org Chem 2008:4157–4168

    Article  CAS  Google Scholar 

  17. Willy B, Rominger F, Müller TJJ (2008) Synthesis 2008:293–303

    Article  CAS  Google Scholar 

  18. Li J, Wang D, Zhang Y, Li J, Chen B (2009) Org Lett 11:3024–3027

    Article  CAS  PubMed  Google Scholar 

  19. François-Endelmond C, Carlin T, Thuery P, Loreau O, Taran F (2010) Org Lett 12:40–42

    Article  PubMed  CAS  Google Scholar 

  20. Niphakis MJ, Turunen BJ, Georg GI (2010) J Org Chem 75:6793–6805

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Rotzoll S, Willy B, Schönhaber J, Rominger F, Müller TJJ (2010) Eur J Org Chem 2010:3516–3524

    Article  CAS  Google Scholar 

  22. Bakulina O, Merkt FK, Knedel T-O, Janiak C, Müller TJJ (2018) Angew Chem Int Ed 57:17240–17244

    Article  CAS  Google Scholar 

  23. Willy B, Müller TJJ (2008) ARKIVOC 2008:195–208

    Google Scholar 

  24. Willy B, Muller TJJ (2009) Curr Org Chem 13:1777–1790

    Article  CAS  Google Scholar 

  25. Gers-Panther CF, Müller TJJ (2016) Adv Heterocycl Chem 120:67–98

    Article  CAS  Google Scholar 

  26. Whittaker RE, Dermenci A, Dong G (2016) Synthesis 48:161–183

    CAS  Google Scholar 

  27. Wu X-F, Neumann H, Beller M (2010) Chem Eur J 16:12104–12107

    Article  CAS  PubMed  Google Scholar 

  28. Wu X-F, Neumann H, Beller M (2011) Chem Soc Rev 40:4986–5009

    Article  CAS  PubMed  Google Scholar 

  29. Gadge ST, Bhanage BM (2014) RSC Adv 4:10367–10389

    Article  CAS  Google Scholar 

  30. Aronica LA, Giannotti L, Tuci G, Zinna F (2015) Eur J Org Chem 2015:4944–4949

    Article  CAS  Google Scholar 

  31. Chavan SP, Varadwaj GBB, Parida K, Bhanage BM (2015) Appl Catal A 506:237–245

    Article  CAS  Google Scholar 

  32. Gautam P, Bhanage BM (2016) ChemistrySelect 1:5463–5470

    Article  CAS  Google Scholar 

  33. Albano G, Morelli M, Aronica LA (2017) Eur J Org Chem 2017:3473–3480

    Article  CAS  Google Scholar 

  34. Aronica LA, Albano G, Giannotti L, Meucci E (2017) Eur J Org Chem 2017:955–963

    Article  CAS  Google Scholar 

  35. Gautam P, Tiwari NJ, Bhanage BM (2019) ACS Omega 4:1560–1574

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  36. Tykwinski RR (2003) Angew Chem Int Ed 42:1566–1568

    Article  CAS  Google Scholar 

  37. Chinchilla R, Nájera C (2007) Chem Rev 107:874–922

    Article  CAS  PubMed  Google Scholar 

  38. Doucet H, Hierso J-C (2007) Angew Chem Int Ed 46:834–871

    Article  CAS  Google Scholar 

  39. Chinchilla R, Nájera C (2011) Chem Soc Rev 40:5084–5121

    Article  CAS  PubMed  Google Scholar 

  40. Karak M, Barbosa LCA, Hargaden GC (2014) RSC Adv 4:53442–53466

    Article  CAS  Google Scholar 

  41. Gholinejad M, Ahmadi J, Nájera C (2016) ChemistrySelect 1:384–390

    Article  CAS  Google Scholar 

  42. Petuker A, El-Tokhey M, Reback ML, Mallick B, Apfel U-P (2016) ChemistrySelect 1:2717–2721

    Article  CAS  Google Scholar 

  43. Evangelisti C, Balerna A, Psaro R, Fusini G, Carpita A, Benfatto M (2017) ChemPhysChem 18:1921–1928

    Article  CAS  PubMed  Google Scholar 

  44. Liu Y, Blanchard V, Danoun G, Zhang Z, Tlili A, Zhang W, Monnier F (2017) Van Der Lee A, Mao J, Taillefer M. ChemistrySelect 2:11599–11602

    Article  CAS  Google Scholar 

  45. Albano G, Aronica LA, Biver T, Detti R, Pucci A (2018) ChemistrySelect 3:1749–1754

    Article  CAS  Google Scholar 

  46. Alonso DA, Baeza A, Chinchilla R, Gómez C, Guillena G, Pastor IM, Ramón DJ (2018) Catalysts 8:202

    Article  CAS  Google Scholar 

  47. Atobe S, Masuno H, Sonoda M, Suzuki Y, Shinohara H, Shibata S, Ogawa A (2012) Tetrahedron Lett 53:1764–1767

    Article  CAS  Google Scholar 

  48. Chuang D-W, El-Shazly M, Balaji DB, Chung Y-M, Chang F-R, Wu Y-C (2012) Eur J Org Chem 2012:4533–4540

    Article  CAS  Google Scholar 

  49. Hwang S, Bae H, Kim S, Kim S (2012) Tetrahedron 68:1460–1465

    Article  CAS  Google Scholar 

  50. Likhar PR, Subhas MS, Roy M, Roy S, Kantam ML (2008) Helv Chim Acta 91:259–264

    Article  CAS  Google Scholar 

  51. Santra S, Ranjan P, Bera P, Ghosh P, Mandal SK (2012) RSC Adv 2:7523–7533

    Article  CAS  Google Scholar 

  52. Loganathan RK, Ramachandra SN (2017) Shekharappa, Sureshbabu VV. ChemistrySelect 2:8059–8062

    Article  CAS  Google Scholar 

  53. Santra S, Dhara K, Ranjan P, Bera P, Dash J, Mandal SK (2011) Green Chem 13:3238–3247

    Article  CAS  Google Scholar 

  54. Hossain S, Park J-H, Park M-K, Jin M-J (2013) J Korean Chem Soc 57:411–415

    Article  CAS  Google Scholar 

  55. Bakherad M, Keivanloo A, Bahramian B, Kalantar Z, N. Ashrafi F (2011) Lett Org Chem 8:364-367

  56. Aronica LA, Caporusso AM, Tuci G, Evangelisti C, Manzoli M, Botavina M, Martra G (2014) Appl Catal A 480:1–9

    Article  CAS  Google Scholar 

  57. Buckley S (2002) Speciality Chemicals Magazine October 2002:12-13

  58. Jiang X, Sclafani J, Prasad K, Repič O, Blacklock TJ (2007) Org Process Res Dev 11:769–772

    Article  CAS  Google Scholar 

  59. Colacot TJ (2008) Top Catal 48:91–98

    Article  CAS  Google Scholar 

  60. Pink CJ (2008) Wong H-t, Ferreira FC, Livingston AG. Org Process Res Dev 12:589–595

    Article  CAS  Google Scholar 

  61. Welch CJ, Leonard WR, Henderson DW, Dorner B, Childers KG, Chung JYL, Hartner FW, Albaneze-Walker J, Sajonz P (2008) Org Process Res Dev 12:81–87

    Article  CAS  Google Scholar 

  62. Frankham J, Kauppinen P (2010) Platinum Met Rev 54:200–202

    Article  CAS  Google Scholar 

  63. Kauppinen P, Phillips S (2010) Speciality Chemicals Magazine March 2010:22

  64. Phillips S, Kauppinen P (2010) Platinum Met Rev 54:69–70

    Article  CAS  Google Scholar 

  65. Caporusso AM, Innocenti P, Aronica LA, Vitulli G, Gallina R, Biffis A, Zecca M, Corain B (2005) J Catal 234:1–13

    Article  CAS  Google Scholar 

  66. Albano G, Evangelisti C, Aronica LA (2017) ChemistrySelect 2:384–388

    Article  CAS  Google Scholar 

  67. Biffis A, Centomo P, Del Zotto A, Zecca M (2018) Chem Rev 118:2249–2295

    Article  CAS  PubMed  Google Scholar 

  68. Chen J-S, Vasiliev AN, Panarello AP, Khinast JG (2007) Appl Catal A 325:76–86

    Article  CAS  Google Scholar 

  69. Joucla L, Cusati G, Pinel C, Djakovitch L (2009) Appl Catal A 360:145–153

    Article  CAS  Google Scholar 

  70. Beaumont SK (2012) J Chem Technol Biotechnol 87:595–600

    Article  CAS  Google Scholar 

  71. Dighe MG, Lonkar SL, Degani MS (2013) Synlett 24:347–350

    Article  CAS  Google Scholar 

  72. Turáková M, Králik M, Lehocký P, Pikna Ľ, Smrčová M, Remeteiová D, Hudák A (2014) Appl Catal A 476:103–112

    Article  CAS  Google Scholar 

  73. Hosokawa S, Teramoto K, Motoyama Y (2016) ChemistrySelect 1:2594–2602

    Article  CAS  Google Scholar 

  74. Hamlin JE, Hirai K, Millan A, Maitlis PM (1980) J Mol Catal A 7:543–544

    CAS  Google Scholar 

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Authors and Affiliations

  1. Dipartimento di Chimica e Chimica Industriale, Università di Pisa, Via Giuseppe Moruzzi 13, 56124, Pisa, Italy

    Gianluigi Albano, Salvatore Interlandi & Laura Antonella Aronica

  2. Consiglio Nazionale delle Ricerche – Istituto di Scienze e Tecnologie Molecolari (CNR-ISTM), Via Gaudenzio Fantoli 16/15, 20138, Milan, Italy

    Claudio Evangelisti

Authors
  1. Gianluigi Albano
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  2. Salvatore Interlandi
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  3. Claudio Evangelisti
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  4. Laura Antonella Aronica
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Correspondence to Laura Antonella Aronica.

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10562_2019_2959_MOESM1_ESM.docx

Detailed experimental procedures and NMR spectra of all synthesized compounds are available online in the Electronic Supplementary Materials. Supplementary material 1 (DOCX 3336 kb)

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Albano, G., Interlandi, S., Evangelisti, C. et al. Polyvinylpyridine-Supported Palladium Nanoparticles: A Valuable Catalyst for the Synthesis of Alkynyl Ketones via Acyl Sonogashira Reactions. Catal Lett 150, 652–659 (2020). https://doi.org/10.1007/s10562-019-02959-5

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  • DOI: https://doi.org/10.1007/s10562-019-02959-5

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